Issue 24, 2014

Improved hemicryptophane hosts for the stereoselective recognition of glucopyranosides

Abstract

Four new enantiomerically and diastereomerically pure hemicryptophane hosts (M-SSS-2/P-SSS-2 and M-RRR-2/P-RRR-2 pairs) were designed for the recognition of sugar derivatives. Their absolute configuration was determined from the circular dichroism spectra and DFT calculations. The host molecules were then used for the stereoselective recognition of glucopyranosides. Binding constants were obtained from 1H NMR titration experiments showing an increase of affinity for this class of receptors, associated with an improved diastereo- and enantio-differentiation.

Graphical abstract: Improved hemicryptophane hosts for the stereoselective recognition of glucopyranosides

Supplementary files

Article information

Article type
Paper
Submitted
21 Jan 2014
Accepted
10 Mar 2014
First published
11 Mar 2014

Org. Biomol. Chem., 2014,12, 4211-4217

Author version available

Improved hemicryptophane hosts for the stereoselective recognition of glucopyranosides

A. Schmitt, O. Perraud, E. Payet, B. Chatelet, B. Bousquet, M. Valls, D. Padula, L. Di Bari, J. Dutasta and A. Martinez, Org. Biomol. Chem., 2014, 12, 4211 DOI: 10.1039/C4OB00156G

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